GB1020807A - Thionothiol-phosphoric and -phosphonic acid esters and process for the production thereof - Google Patents
Thionothiol-phosphoric and -phosphonic acid esters and process for the production thereofInfo
- Publication number
- GB1020807A GB1020807A GB32255/64A GB3225564A GB1020807A GB 1020807 A GB1020807 A GB 1020807A GB 32255/64 A GB32255/64 A GB 32255/64A GB 3225564 A GB3225564 A GB 3225564A GB 1020807 A GB1020807 A GB 1020807A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- phosphoric
- phosphonic acid
- thionothiol
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 alkyl radical Chemical group 0.000 abstract 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 150000003008 phosphonic acid esters Chemical class 0.000 abstract 3
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 3
- 241001124076 Aphididae Species 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 241000239290 Araneae Species 0.000 abstract 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 abstract 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises thionothiol phosphoric and phosphonic acid esters of the formula <FORM:1020807/C2/1> wherein R is an alkyl radical containing up to four carbon atoms, R1 is an alkyl or alkoxy radical containing up to four carbon atoms, R2 and R3 are hydrogen atoms or together stand for a fused benzene ring, R1 is a hydrogen atom or is a methyl radical if R2 and R3 stand for a fused benzene ring. They may be produced by reacting an ester of the formula <FORM:1020807/C2/2> in which R, R1 and X have the same meanings as above and Hal is a halogen atom with a 2-mercapto-pyridine or quinoline of the formula <FORM:1020807/C2/3> in which R1, R2 and R3 have the same meanings as above or with the use of the mercapto compound in the form of a salt, preferably an alkali metal salt. The reaction is preferably carried out in the presence of an inert organic solvent or diluent and, where the free mercapto compound is used in the presence of an acid-binding agent. Preferred solvents are aliphatic alcohols and ketones, such as methanol, ethanol, acetone, methyl ethyl ketone, methyl isopropyl and methyl isobutyl ketone and dimethyl formamide while alkali metal alcoholates and carbonates e.g. sodium methylate sodium ethylate and potassium carbonate are satisfactory acid-binding agents. Suitable reaction temperatures are between 20 DEG C. and 80 DEG C. Catalytic amounts of alkali metal iodide may also be used. The thionothiol phosphoric and phosphonic acid esters may be used as the active ingredient in pesticidal compositions (see Division A5).ALSO:Thionsthiol phosphoric and phosphonic acid esters of the formula: <FORM:1020807/A5-A6/1> wherein R is an alkyl radical containing up to four carbon atoms, R1 is an alkyl or alkoxy radical containing up to four carbon atoms. R2 and R3 are hydrogen atoms or together stand for a fused benzene ring, and R1 is a hydrogen atom or is a methyl radical when R2 and R3 stand for a fused benzene ring atom (see Division C2) are used either alone or in combination with a solid or liquid diluent or carrier as pesticides. They may also be used in combination with each other or with known insecticides and/or fertilisers. Examples of solid carriers are talc, chalk, bentonite and clay and as liquid carriers water, if necessary with commercial emulsifiers, alcohols, especially methanol or ethanol, ketones, especially acetone and methyl ethyl ketone, and liquid hydrocarbons may be used. An example describes the use of varying concentrations of O,O-diethyl-thionothiol-phosphoric acid-s-[pyridyl-(2)-mercepto-methyl] ester and ethylthionothiol-phosphonic acid-o-ethyl-s-[pyridyl-(2)-mercapto-methyl]ester against aphids and spider miles on heavily invested beanplants, caterpillars on white cabbage, flies on drip wet filter papers and oat aphids on oat plants. The aqueous dilutions of the active compounds are prepared by mixing them with dimethyl formamide as solvent, a benzyl hydroxy diphenyl polyglycol ether as emulsifier and finally diluting the premixture with water. Application of the compositions may be by spraying or by watering the soild without wetting the leaves of the plants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF40454A DE1206903B (en) | 1963-08-08 | 1963-08-08 | Process for the production of thiol- or thionothiolphosphorus - (- phosphonic) acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1020807A true GB1020807A (en) | 1966-02-23 |
Family
ID=7098239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32255/64A Expired GB1020807A (en) | 1963-08-08 | 1964-08-07 | Thionothiol-phosphoric and -phosphonic acid esters and process for the production thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3320261A (en) |
| BE (1) | BE651553A (en) |
| CH (1) | CH440275A (en) |
| DE (1) | DE1206903B (en) |
| GB (1) | GB1020807A (en) |
| NL (1) | NL6408976A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2003141A1 (en) * | 1970-01-24 | 1971-07-29 | Bayer Ag | 2-Oxo-dihydroquinoline thionophosphorus (phosphonic) acid esters and process for their preparation |
| US4462994A (en) * | 1981-05-19 | 1984-07-31 | Nissan Chemical Industries, Inc. | N-Containing heterocyclic ring-substituted O-arylphosphate derivatives, preparation thereof, and insecticides, acaricides and nematocides containing said derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2706194A (en) * | 1951-05-14 | 1955-04-12 | Shell Dev | Esters of phosphonic acids |
| US2818366A (en) * | 1955-09-21 | 1957-12-31 | Monsanto Chemicals | Method of controlling nematodes employing haloalkyl phosphonic dihalides |
| US2906661A (en) * | 1958-03-18 | 1959-09-29 | Monsanto Chemicals | Treating agricultural soils with propargyl phosphorothioates |
| NL237242A (en) * | 1958-03-18 | 1900-01-01 | ||
| US2961445A (en) * | 1958-08-25 | 1960-11-22 | Monsanto Chemicals | Pyridylalkylthioalkyl and oxyalkyl phosphorothioates |
| CH387620A (en) * | 1960-07-08 | 1965-02-15 | Sandoz Sa | Process for preparing esters containing phosphorus |
-
1963
- 1963-08-08 DE DEF40454A patent/DE1206903B/en active Pending
-
1964
- 1964-07-09 CH CH903564A patent/CH440275A/en unknown
- 1964-08-05 NL NL6408976A patent/NL6408976A/xx unknown
- 1964-08-07 BE BE651553D patent/BE651553A/xx unknown
- 1964-08-07 GB GB32255/64A patent/GB1020807A/en not_active Expired
- 1964-08-10 US US388688A patent/US3320261A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE651553A (en) | 1965-02-08 |
| US3320261A (en) | 1967-05-16 |
| DE1206903B (en) | 1965-12-16 |
| CH440275A (en) | 1967-07-31 |
| NL6408976A (en) | 1965-02-09 |
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